


To Rochester from Boston

by wigglebox



Category: Supernatural
Genre: Alternate Universe - College/University, Graduate School, M/M, Sex Tapes, Top Dean Winchester, Trans Castiel (Supernatural), Trans Male Character, cos I'M LEAAAVING ON A JET PLANE
Language: English
Status: Completed
Published: 2019-04-26
Updated: 2019-04-26
Packaged: 2020-02-04 16:40:44
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,249
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18608440
Author URL: https://archiveofourown.org/users/wigglebox/pseuds/wigglebox
Summary: Sometimes you got to treat yo' self, especially when your long-term boyfriend is leaving for several months.





	To Rochester from Boston

The sex tape was Cas’s idea, but it was Dean who executed it to perfection. 

Cas was heading to Minnesota for four months to complete a clerkship at the Mayo Clinic as part of his graduate degree. They hadn’t been apart for that long since they started their relationship five years prior during undergrad at Boston University. 

Dean wasn’t worried for their relationship, but he didn’t know what to do with himself for all those months. He still had to stay in Boston and finish his own graduate degree in mechanical engineering. Otherwise, he’d hop a plane out to bumfuck nowhere Minnesota as well. 

He hardly watched porn in the years since seeing Cas, and he didn’t have plans on going back. It didn’t match up to what they were both capable of, and just seemed like a colossal waste of time. While lamenting this to Cas one night as the packing began, Cas came up with his brilliant idea. 

“Do we film it on our phone?” Dean asked, already seeing if he had enough space. 

“We could. I would just take iCloud off and airdrop capabilities off too. I don’t want it getting around.” Cas tossed a few folded button downs into the suitcase. 

Dean went through his settings, ticking every box he could think of off.

“Should I delete it when you get back?”

Cas shook his head, “I plan on sending you things, and I know you plan on sending me things. We will probably wind up keeping them but we can reassess after.”

Dean did plan on sending more videos to Cas, already planning on where he’d film them. He wondered if Cas thought the same thing. The science library was their favorite “public” space. Maybe Dean should start there. 

Cas had a sex drive that made Dean feel like an old man sometime. Cas once told Dean that it used to be worse, even before transitioning, but everything changing made it spike. Eight years on, things were settling back to normal but normal for Cas was still above average for Dean.

Dean considered it nothing but wonderful.

It took several months, almost a year for Cas to come out to Dean, only spurred on by the fact that he accidentally fell for the man during their study group sessions. It turned out the feelings were mutual, but before Cas allowed the relationship to go any further, he explained to Dean that if he was expecting another dick down there, he’d be mistaken. 

Dean remembered watching, both amused and shocked, when Cas undid his pants while laying on his dorm bed, and drew out a packer. The information didn’t process in Dean’s brain right away, his own dick more focused on the fact Cas looked _delightful_ laid back against the pillows. 

But Dean’s brain eventually caught up with with and he listened patiently when Cas explained fully his past, his present, and what he wanted from the future with Dean. 

As for Dean, he had never been with a transgendered person before, and was pretty much in the dark. That night, instead of sex, they talked for hours. Dean didn’t want to lose the first stable friendship he had in a long time because he was an idiot. They worked together through the ups and downs and side to sides of their budding relationship. The more that Dean peeled back the layers of Cas’s life, the more enticing and entrancing he found the man. 

It was a relationship for firsts with Dean, and even five years later, he still found himself surprised. 

Like tonight when Cas suggested a sex tape. 

Dean watched Cas turn to the closet and take out a couple hangers with slacks dangling from the clips. He was going to miss him. 

“Are you gonna do any doctor roleplaying for me out there?” Dean asked casually, enjoying the sight of Cas freezing with the clothes in his hands, his back tensing up. It really didn’t take much to get Cas going. He didn’t know if they were going to make the video tonight, but they may as well. They can make three tapes for all he cared, one for each night until Cas left on Monday. 

Cas turned slightly to catch Dean’s gaze over his shoulder, his cheeks already revealing a faint flush, “Only if you’re good.”

Dean felt the faint lickings of fire in his groin as Cas turned back to his closet, grabbing a few more shirts. 

When he returned to the edge of the bed, Dean just watched him. Watched every movement. Cas had a mouth to him and challenged Dean often as part of their little ‘game’. Who would break first? It worked every time, without fail, over the course of their relationship. Cas had some sort of magic spell over Dean, and Dean wasn’t complaining. 

Licking his lips, and moving back more onto their bed, he leaned back,resting on his elbows. All he had on was a pair of flannel pj bottoms. Flimsy ones at that. 

Cas stopped folding the clothes, lifted his head, and pursed his lips. 

“We’re seriously doing this now? I haven’t finished packing yet.” 

Dean pouted, “You have all weekend to pack.”

“You think we’re going to make it out of bed this weekend?” Cas challenged Dean, and Dean knew the answer. No. No they will probably not leave their bed. 

Instead of answering, Dean only rocked his hips from side to side, delicate soft movements that rustled the fabric of the bed spread below him. 

“We can always make more than one.” 

Cas watched, his eyes going dark. Dean kept moving while finally opening his mouth to speak, tilting his head back at the ceiling, exposing his neck.

“I’m just saying if I was as horny as you are on a daily basis, I’d want to get as much dick in me before I had to leave for four months.”

Cas closed his eyes at that, leaning down and bracing himself on the sides of the suitcase. Dean grinned. He was winning. 

Dean’s own dick was beginning to rise to the occasion, pushing against the fabric of his pajama pants ever so slightly. He glanced down at it before back at Cas. 

“I think it wants you.”

They locked eyes for half a second before they moved into action simultaneously:

Dean scrambled back to get his phone which was charging on the bed stand; Cas slammed the front of the suitcase down and practically tossed it off the bed, contents thrown around; Dean trying to swipe up to get the video option going with shaking fingers; Cas crawling over to him on the bed like a predator who found its prey. 

Dean finally got the video to start recording, but Cas took the phone from his hands. He stopped it, flipped the camera horizontal, and started again. 

“This way you can watch it on the TV,” he muttered while he straddled Dean’s hips, handing him the phone. Dean barely noticed as he felt through the thin layers of flannel pajamas they both wore the hot heat that was waiting for him. He wanted it. 

He stood the camera up on his chest, hands holding it in place. With two fingers, he zoomed into where Cas and he met at the groin. Automatically, Cas bent over and placed his hands on the bed beside Dean. He started to shift his hips back and forth over the hard cock underneath him. Dean watched through the phone’s screen, his breath becoming shallower with every swipe - forward and back, forward and back -

Cas continued for a few minutes, setting up a rhythm while waking Dean up. Dean himself was fascinated by the image on the phone. He zoomed out to catch Cas’s look of concentration before going back down. He could things so much closer now than he usually did. 

After a bit, as Cas’s hips went on a slight upwards angle when he slid forward, Dean could see the light fabric start to grow darker already. 

“I haven’t even touched you yet and you’re already this wet?” Dean breathed, finally tearing his eyes away from the screen. Cas’s own eyes were closed in concentration, his head hanging loose from his shoulders as he started to increase the pressure. He could only grunt an affirmative as he continued to push down, back and forth, push down -- 

This was one of Dean’s favorite parts. It took absolutely no time for Cas to get himself in a position where he could just be tossed against a wall, onto a couch, bed, chair -- whatever -- and just get completely and utterly fucked. Sometimes, the most minimal effort was needed, Dean once having Cas stifle an orgasm in the middle of the dining hall several years ago just by rubbing him softly through his pants. 

Soaking wet was one thing, but one of the things Dean loved was that Cas’s clit was _large_. He was told early on why that was, and Dean gave a silent prayer of thanks because it was one of the biggest turn ons ever. Cas described how at first, it would rub against the fabric of his underwear and pants and it was too annoying to be turned on by it. Eventually he learned how to gain control. 

But, just like Dean’s cock, the clit also always stood erect and ready to go. Dean once asked what it felt like. He had only been with one other person who had a vagina, and her clit was small, difficult to find with her anatomy, and Dean inexperienced. She didn’t enjoy the sex as much, and dumped Dean after only two months together. Cas had a hard time describing it in a way that Dean could relate to, only eventually something about sparks of pleasure radiating out in strong pulses. He also said due to the transition, his orgasms were more intense than pre-T, making his legs and torso tingle, not just his pelvis. After that statement, Dean told Cas to prove it. 

Dean wanted to use both of his hands, so he mustered the strength to sit up slightly and propped the phone up against the lamp on the table next to him, zooming back out just enough so they stayed in frame, but weren’t too far away. 

When he looked back, he saw the dark patch had grown.

“Alright, time to see what’s going on down there,” Dean stated matter-of-factly before surging upwards, twisting, and pushing Cas down into the mattress so his head rested on one of the pillows. All Cas could do was moan, and continue to wriggle his hips while his knees bent, seeking _something_. His eyes were still clamped shut. 

“Hey, I want to see your eyes — open back up,” Dean ordered, tapping on the side the knee next to him. Cas obliged, and Dean exhaled sharply at the dark, blown out pupils that replaced the blue. 

Without another word, he grabbed the hem of Cas’s pajama bottoms and tugged, Cas lifting his hips obediently. It wasn’t going to be one of those nights where he tried to tease Dean as much as he could: Cas clearly had been waiting for this all day. 

As Dean pulled away the bottoms which showed only a little bit of the wet patch, he was instead greeted with light blue underwear that had been turned a navy blue between Cas’s legs. 

“Jesus Christ,” Dean breathed. The underwear was tight, and slightly ridden up farther than usual. Cas not wearing boy shorts that night. Dean could see the bump between Cas’s legs. He wanted to run a finger alongside it, but held himself off. 

He leaned over and snatchd the phone up, flipping the screen so it was back on Cas, who was now practically panting. He kept trying to move his hips closer to Dean but Dean held him off. 

Instead, Dean lowered the phone. He didn’t watch the screen this time, instead following his index finger in real time as he traced a delicate line from the top to the bottom of the ridge where he stayed there, making tiny circles with his finger tip. 

The reaction was priceless, and now on camera. 

Cas twitched almost violently, bucking his hips up trying to get more pressure. His back arched slightly, and his head tilted to the side as a long, deep groan bubbled up. Dean hardly breathed as he brought the camera back up, resting his wrist on Cas’s knee, allowing the camera to take in the sight before him as his free finger and hand continued to rub. . 

This was a _fantastic_ idea. 

Dean pulled his free hand away, causing Cas to inhale sharply. Without giving Cas enough time to think, Dean slid his finger into a lower section of the underwear. 

Bringing the camera back down again, he ran the back of his finger which rested against the hot, swollen flesh under the fabric up and down, feeling the fire. When he brought his finger back up, he twisted it slightly, and made contact with Cas’s clit once more, no barrier between them now. 

Cas whined and tightened his knees around Dean’s sides. Dean didn’t make any movements, just allowing his finger to rest. It was amazing what just one finger could do when Cas was in his zone. 

Dean pulled on the fabric so it made a gap, revealing what hid in the shadows. He shifted the phone to rest against Cas’s pelvis, the camera lense right up next to the newly opened space. Dean didn’t know what it was showing, but if it was showing anything that he was feeling on his own, then it was going to be one of the hottest things he’ll ever watch. 

He withdrew his finger, allowing the camera to catch the mess that remained on it. He made the camera follow him now to the elastic band resting against Cas’s hot skin. Dean pulled, gentle but affirmative, until it started to give way some. But he struggled, and he didn’t want to put the camera down. 

“Take these off,” Dean ordered, bringing his free hand back up to the camera to steady it. He was starting to shake, “Slowly.” 

Without a word, Cas hooked his fingers into his underwear and pulled down. Dean zoomed in on the sight as they peeled away. The image of that combined with Cas’s soft panting and hard nipples against a flushed chest was pushing Dean to the edge already. He couldn’t stop watching. 

Cas shifted so his legs were free to slide the fabric off and tossed them to the side. 

Dean kept the camera steady on the glistening, already dripping wet prize beneath him before panning up to Cas’s bright pink face. 

“I’ll never understand how you get like this so fast without any effort from me,” Dean said, wonderment in his voice. Cas’s sex crazed face melted into a soft smile. 

“Take is as a compliment,” Cas breathed, chest moving up and down at an uneven pace, “You don’t even have to touch me for me to get off on you.”

“Well, right now, the only way you’re getting off is on my thigh because I’m about to burst and I don’t want it over just yet.”

Without waiting for Cas to respond, Dean handed him the phone. Cas held it while watching Dean discard his own bottoms and underwear off, finally free. Dean felt hot under the camera’s gaze. Maybe that’s why Cas was so hot to trot already. 

Dean bent over Cas, placing his hands on either side of his shoulders. He lowered his head, planted a quick kiss, then moved his right leg so it jammed right up against Cas’s slick pussy, applying pressure directly on his clit now. 

Cas almost dropped the phone but managed to save it. Dean didn’t know what the sight looked like, but it felt amazing. His own cock brushed against the skin of Cas’s pelvis, allowing soft tendrils of pleasure to spiral up. 

Dean held himself over Cas as Cas slid his hips up and down. The camera was shaking but Dean hoped it was capturing the movements. When Cas shifted his hips down, Dean felt the wetness on his thigh cool ever so slightly before being covered once more. He felt the rock hard clit digging into his skin, dragging up and down, 

In a way, Dean was jealous of that. His dick was there because it had to be. It was for making babies and taking a piss. But Cas had a magic button that was purely for pleasure. It swelled much like a dick but it didn’t shoot anything out when done. It just stayed there, waiting to deliver whatever waves of lust it could to its host before obediently retreating, waiting for its next opportunity. 

It took only a few swipes of Cas’s hips for the man to come. His hips shot upwards, then ground back down on Dean’s thigh so hard, Dean almost lost his balance. Dean felt Cas shake, and the clit pulse against him as Cas kept rubbing himself in short, shallow motions. He whine, moaned, and whimpered all the way through it, but to Dean’s delight, kept the phone up. 

Cas’s muscles finally relaxed, and his hips fell back to the bedspread, legs falling open. Dean breathed steady for a few months with his eyes closed before opening them, gazing down at the man below him. Blissed out sex face, check. Muscle weakness? Check. Breathing slowly stabilizing? Check. 

Dean was told about and witnessed many occasions where Cas can come nearly six times in one sitting. This one was a small one. This one was them both just getting started. 

Dean plucked the camera from Cas’s limp hands and sat back. It was his turn now. 

The camera tilted down at the mess between Cas’s legs. Dean held the shot for as long as he physically could. With Cas’s thighs spread out, Dean could see everything. Everything that kept twitching, moving, and waiting for something to fill it. Cas’s clit was still hard as a rock, even more swollen than before. The first orgasm was thankfully not enough. 

Dean didn’t even attempt to hold Cas’s legs against him. They’d start working again soon. Instead, he held the camera steady with one hand and used his free hand to finagle the action he needed. He grabbed the tip of his cock, just under the head, and brushed it against Cas, up and around whatever was exposed and then up to his clit. It was such an easy target, and the quickest way to get Cas backup and running again. 

Cas sucked in his breath as Dean continued to rub. He moved the camera back and forth between that, and Cas’s face which was now more red instead of pink.

Hips started to move again. Cas wanted more. 

Dean turned the camera back to Cas’s face which was turned to the side.

“What do we say?” he asked. 

Cas mumbled something unintelligible. 

“I’m sorry, what was that?” The teasing was torturing Dean as well as Cas but he wanted to hold out as much as he could. The longer the video, the better it would be in the long run.

Cas still only mumbled, starting to grind his hips again, seeking some sort of relief. 

Dean clicked his tongue and backed off fully, causing Cas to groan in frustration. 

“I said I can’t hear you.” 

“I said FUCK ME!” Cas shouted the last two words, turning his head to glare into the camera. Dean winced. Their upstairs neighbors definitely heard that. Cas’s voice was low, deep and hoarse, like he’d been straining his vocal cords for a day instead of a half hour. 

Dean obliged, started to slip in to the velvety fire. He went as slow as he could, allowing the camera to catch it all. 

When Dean finally bottomed out, he had to squeeze his eyes shut, trying to mentally block himself from just coming right there and then. That would have been pretty lame. He had a good refractory period but he wanted this one video to last as long as it could. 

When he came to, he realized that Cas was still glaring at him, and his cock was being squeezed, released, squeezed, released. Cas clearly didn’t care how long the video was. He just wanted to get railed. 

Fine. 

Dean once again placed the camera on the nightstand, flipping the camera so it faced them. The sight was beautiful. Cas himself even stopped and looked at how they appeared on screen. They never saw themselves in a third person view like that. 

“Holy shit,” Cas muttered, unable to take his eyes off them. That was when Dean realized that they made the right decision in making the video. 

Before they got too lost, Dean pulled all the way back out, causing Cas to cry out in protest. Dean grabbed Cas by the hips, and forced him over onto his side. Cas got the hint and moved instantly onto his stomach. 

Dean gave up on his efforts to go slow. It was time for some rough and dirty. 

Fingers digging into Cas’s flesh, Dean hoisted Cas’s backside up, flashing everything that Dean ever wanted. Without saying a single word, Dean thrust back in without any push back. 

A deep, soul shattering groan ricocheted through Cas’s body, and he seized up around Dean immediately, setting him free a moment later. 

Dean didn’t look at Cas though as he started to fuck him in earnest, pulling out and throwing himself in at a steady speed. Instead, he looked right at the camera lense on the phone. If Cas was going to be watching this, Dean wanted him feeling like he was staring at him through the computer screen, watching everything Cas did in private. 

He realized the video was also for himself, but just the knowledge of Cas getting off to this amatuer porno they just made would be satisfactory enough. Besides, Cas promised him more videos while he was gone. 

Dean shifted his hips slightly at an angle, and picked up his pace. He wondered if the noise of skin hitting skin would pick up on the phone’s microphone. 

An idea came to him mid-thrust and he angled himself even more, still in Cas, to grab the phone once more. As he did, Cas shouted something, and snapped his hips, inward, away from Dean, leaving him out and exposed. Dean looked back and saw Cas quivering on the mattress below him, his hips moving up and down against the fabric on their own. Before Dean could question what happened, Cas lifted himself back up and started to fuck himself on Dean’s cock, all while Dean tried to process the quick turn of events. 

But, as Dean moved to put the phone down underneath them to captured a different angle, he saw what happened, and was pissed at himself for missing it. 

The bedspread below was soaked. Cas had sharp and fast, squirting all over the blanket underneath him. 

This was a new trick. 

The breath knocked out of him, and feeling the tidal wave emerging inside him, he placed the phone underneath on the wet fabric. He wanted Cas to do it again, but knew if he did, the phone would be ruined. 

It was a chance he took. 

Cas was on his third orgasm now, slamming his hips backwards trying to get more of Dean’s cock in that Dean didn’t have available. Dean met Cas’s force once, twice, three times before feeling himself spill inside. Blood rushed to his ears, and the white light had returned. Everything felt faint, and any noises around him dulled to a high pitched tone. 

Cas went through a few aftershocks, squeezing again and again on Dean’s cock, making him wince slightly. It felt good though. He circled his hips around to make sure everything was settled before slowly starting to pull out. 

Cas was babbling incoherently, quiet and to himself. Dean slipped free, hoping the camera beneath them captured the remnants of come that still attached itself to the tip of his cock. He didn’t realize how much actually came out of him until he reached down to grab the phone, and saw some of it sliding back out. 

“Holy shit,” Dean muttered. He’d seen his come it before plenty of times but this time he wanted to get it on camera. Cas never got to see it, and now he could witness what exactly Dean saw after a good fuck. 

Everything on display from Cas was still an angry, swollen red. One more time, because he couldn’t help himself, Dean pressed his finger against the clit. He always loved the reaction it gave him as Cas would cry out in both agony and pleasure. At some point, it would go back down slightly and Cas would have had enough. But for now it was an amazing sight to behold. 

“I can’t wait for you to see this,” Dean said, still training the camera lense on Cas’s swollen underside. 

“How many of these did you say we could make?” Cas asked, breathless and stifled as he had pulled part of the pillow over his head. 

“As many as you want.” 

Cas nodded and collapsed onto his side, lifting a bent knee up. 

“Start a new one. I’m not done yet.” 

**Author's Note:**

> This was written for the following smut prompts requested by Anon on my tumblr (wigglebox)  
> “I haven’t even touched you and you’re already this wet”  
> “The only way you’re getting off is on my thigh.”
> 
> \--  
> I was out of my element writing this because I've never written trans characters before, but the prompts indicated, to me at least, that it was just meant to be written like that. 
> 
> I was helped along by [Wuya626 on tumblr](https://wuya626.tumblr.com/), who patiently answered my questions so I made sure not to write something accidentally offensive or completely inaccurate. 
> 
> Obviously, some liberties were taken because it's still straight up porn lol. 
> 
> Thank you for reading!


End file.
